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Reactive intermediates from nitrosamines.

M C Archer

    Advances in Experimental Medicine and Biology
    |January 1, 1981
    PubMed
    Summary
    This summary is machine-generated.

    N-nitrosodi-n-propylamine metabolism in rats forms DNA adducts. DNA alkylation occurs via bimolecular reactions, not free cations, for N-propylguanine formation.

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    Area of Science:

    • Biochemistry
    • Toxicology
    • Molecular Biology

    Background:

    • N-nitrosamines are known carcinogens.
    • Understanding their metabolic activation and DNA interaction is crucial for risk assessment.

    Purpose of the Study:

    • To elucidate the metabolic pathways of N-nitrosodi-n-propylamine.
    • To investigate the mechanism of DNA alkylation by this compound and its metabolites.

    Main Methods:

    • Incubation of N-nitrosodi-n-propylamine with isolated rat liver fractions.
    • Administration of N-nitrosodi-n-propylamine and its metabolites to rats.
    • Analysis of DNA adducts in hepatic DNA using chromatography and mass spectrometry.

    Main Results:

    • Metabolism yielded n-propanol and isopropanol, suggesting initial alpha-hydroxynitrosamine formation and potential carbonium ion generation.

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  • In vivo, 7-n-propylguanine was formed in hepatic DNA, but not 7-isopropylguanine, indicating DNA nucleophilic interception before carbocation formation.
  • Oxidation produced N-nitroso-2-oxopropylpropylamine, which led to 7-methylguanine and O6-methylguanine in DNA.
  • The ultimate methylating agent remains unidentified.

    • Conclusions:

    • DNA alkylation by N-nitrosodi-n-propylamine in vivo likely proceeds via a bimolecular mechanism, not involving free alkyl cations.
    • Metabolic activation of N-nitrosodi-n-propylamine can lead to both n-propylation and methylation of hepatic DNA.
    • Further research is needed to identify the specific methylating agent responsible for methylation adducts.